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WO1996037491A1 - Derives heterocycliques ayant un groupe hydroxyalkyle phenyle et herbicides - Google Patents

Derives heterocycliques ayant un groupe hydroxyalkyle phenyle et herbicides Download PDF

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Publication number
WO1996037491A1
WO1996037491A1 PCT/JP1996/001363 JP9601363W WO9637491A1 WO 1996037491 A1 WO1996037491 A1 WO 1996037491A1 JP 9601363 W JP9601363 W JP 9601363W WO 9637491 A1 WO9637491 A1 WO 9637491A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkyl
alkyl group
alkoxy
halogen atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP1996/001363
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English (en)
Japanese (ja)
Inventor
Akiyoshi Ueda
Yasuyuki Miyazawa
Masami Koguchi
Isoko Matsumoto
Takashi Kawana
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Soda Co Ltd
Original Assignee
Nippon Soda Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Soda Co Ltd filed Critical Nippon Soda Co Ltd
Priority to AU57785/96A priority Critical patent/AU5778596A/en
Publication of WO1996037491A1 publication Critical patent/WO1996037491A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof

Definitions

  • the present invention relates to novel benzoic acid derivatives, production methods and herbicides. Background technology:
  • Japanese Patent Application Laid-Open No. 19-35776 describes a certain phenoxypyrimidine derivative having herbicidal activity.
  • an object of the present invention is to solve the above-mentioned problems and to provide a herbicide which has excellent herbicidal activity and can be used safely.
  • Japanese Patent Application Laid-Open No. Hei 11-39576 discloses a compound related to the compound of the present invention.
  • WO94 / 17959 discloses the herbicidally active compound represented by the following general formula [1 '] by the present inventors.
  • an object of the present invention is to provide a herbicide that can be synthesized industrially advantageously, has a low dose, is effective, has high safety, and has high crop selectivity.
  • the present invention will be described in detail.
  • the present invention is a compound represented by the general formula [1] and a herbicide.
  • A represents a nitrogen atom or a carbon atom substituted by R 3 ;
  • Z represents an oxygen atom, a sulfur atom, SO or S 0 2,
  • R,, R 2 are each independently hydrogen atom, methyl, Echiru, isopropyl, butyl, such as t- butyl group C, - 6 alkyl group, main butoxy, ethoxy, Purobokishi, iso C,-(! Alkoxy, trifluoro P methoxy, trichloromethoxy, trifluoroethoxy, etc. halo C alkoxy, trifluoromethyl, trichloro, etc., such as propoxy, butoxy, t-butoxy, etc.
  • Halo C alkyl groups such as methyl and trifluoroethyl groups, C ⁇ 6 alkylamino groups such as methylamino, ethylamino, propylamino, isopropylamino and butylamino groups, dimethylamino, methylethylamino, getylamino groups, etc.
  • C 6 alkylthio group such as a di-C alkylamino group, methylthio, ethylthio, propylthio, isopropylthio, and butylthio group
  • a halogen atom such as fluorine, chlorine, and bromine
  • a cyano group such as fluorine, chlorine, and bromine
  • R 3 is a hydrogen atom, methyl, ethyl, isopropyl, butyl, t-butyl, etc.
  • C represents an alkyl group, a halogen atom such as fluorine, chlorine, or bromine, a nitro group, a formyl group, or an acyl group such as an acetyl or propionyl group, and R 2 and R 3 together form a ring May be
  • R “R 5 are each independently hydrogen atom, methyl, Echiru, isopropyl, butyl, t - C i alkyl group such as butyl, cyclopropyl, C cycloalkyl group such as cyclohexyl group cyclopentyl, to consequent opening, Application Benefits Halo C alkyl groups such as fluoromethoxy, trichloromethoxy, trifluoroethoxy, C, 16 alkoxy such as methoxymethyl, methoxethyl, methoxypropyl, ethoxymethyl, ethoxymethyl, ethoxypropyl, etc.
  • C alkyl group Mechiruchiomechi Le, Mechiruchioechiru, methylthiopropyl, Echiruchiomechiru, Echiruchioe chill, C I 6 alkylthio C Bok alkyl group such as E Ji thio propyl, methylation sulfonyl methyl, methylsulfonyl E chill, methylsulfonyl propyl, ⁇ ⁇ tilsuljo 'Rumechiru, E chill sulfonyl E chill, C alkylsulfonyl C alkyl group such as E chill sulfonyl propyl, vinyl, Ariru, C 2, such as crotyl - 6 alkenyl group, Echiniru, C Aruki two Le group such as propargyl group, human Dorokishimechiru, human Dorokishechiru arsenide de proxy C alkyl group such as hydroxycarboxylic propyl, optionally substituted a
  • An optionally substituted phenyl group, halogen atom, 6 alkyl group, C! —Heterocyclic group or halogen atom, C! Represents a benzoyl group which may be substituted with an alkyl group or a C alkoxy group or the like, and R 4 and R 5 may form a ring together;
  • R 6 is a hydrogen atom, d- 6 alkyl group such as methyl, ethyl, isopropyl, butyl, t-butyl group, C cycloalkyl group such as cyclopropyl, cyclopentyl, cyclohexyl group, trifluoromethoxy, trichloromethyl Halo C alkyl groups such as toxic and trifluoroethoxy groups, C ⁇ 6 alkoxy C such as methoxymethyl, methoxyl, methoxypropyl, ethoxymethyl, ethoxymethyl and ethoxypropyl groups!
  • alkylthio-C alkyl groups such as ⁇ -alkyl group, methylthiomethyl, methylthioethyl, methylthiopropyl, ethylthiomethyl, ethylthioethyl, ethylthiopropyl group, methylsulfonylmethyl, methylsulfonylethyl, methylsulfonylpropyl, ethylsulfonylmethyl, E chill sulfonyl E chill, C i, such as E chill sulfonyl propyl - beta ⁇ alkylsulfonyl C, - 6 alkyl group, vinyl, Ariru, C alkenyl group such as crotyl, Echiniru, C alkynyl group such as propargyl group, human !
  • 6 alkoxy group such as in substituted substituted may be may be off group, a halogen atom, Ci-S alkyl groups, C alkoxy group which may be substituted Fuweniru sulfonyl group, etc., a halogen atom, C, - 6 alkyl
  • a heterocyclic carboxy group which may be substituted with a benzoyl group or a halogen atom, a CiB alkyl group, a Ci-6 alkoxy group or the like which may be substituted with a C i - ⁇ alkoxy group,
  • Each Yl ⁇ Y 8 are independently hydrogen or methyl, represents Echiru, propyl, C I 6 alkyl group such as I isopropyl propyl group, and the carbon ring or in two ⁇ also form a heterocyclic ring Good.
  • the compound of the present invention can be produced by the following method.
  • a compound of the general formula [2] (wherein, Ri, R 2 , A, Q, YZ, and n have the same meaning as described above, and X represents bromine or iodine) may be an alkyl lithium (for example, butyl lithium) ), To synthesize aryl lithium by halogen-metal exchange, and then to the general formula [3] (wherein R 4 and R 5 have the same meanings as described above). This compound is subjected to force coupling in a dry organic solvent. Examples of the solvent include THF, ME, ether and the like. The reaction proceeds smoothly under an inert gas atmosphere at a temperature ranging from 178 ° C to room temperature until the reaction is completed.
  • the compound represented by the general formula [2] can be obtained, for example, by the method disclosed in International Application No. JP95 / 012523.
  • a compound of the general formula [2] (wherein, R 2 , A, Z, R 4 and Y 8 represent the same meaning as described above, and X represents bromine or iodine).
  • an alkyllithium such as, for example, aryl-lithium is synthesized by halogen-metal exchange, and then DMF and a dry organic solvent are subjected to force coupling to obtain a compound of the general formula [4a].
  • Solvents that can be used include THF, DME, ether and the like. The reaction is carried out under an inert gas atmosphere until the reaction is completed. Performed at 78 ° C. to room temperature.
  • Alkylating agents such as alkyl halides; acylating agents such as acyl halides and acid anhydrides; alkylsulfonylating agents such as sulfonyl halides and sulfonic anhydrides; arylsulfonylating agents;
  • a thiocarbamoylating agent such as thiocarbamoyl halide or a silylating agent such as silyl halide, etc.
  • the general formula [1] (wherein, R 2 , R 4 , R 5 , A and Z are as defined above) Represents the same meaning.
  • Compounds can be manufactured. -The structure of the compound of the present invention was determined from IR, NMR, MS and the like. ⁇ Example ⁇
  • reaction mixture was poured into ice water, adjusted to pH 3 with dilute hydrochloric acid, and extracted with ethyl acetate.
  • the organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue is treated with benzene-petroleum ether, and crystals of 2- [2-formyl-1- (2- (4,6-dimethoxy-1-2-pyrimidyloxy)) phenyl] tetrahydrobenzoxazole are obtained. 17 g were obtained.
  • Table 1 shows specific examples of the compound of the present invention including the above Examples.
  • u Physical property value is 3 ⁇ 4 or refractive index
  • the compound of the present invention shows a high herbicidal activity under both the soil treatment and the foliage treatment under upland cropping conditions.
  • it contains compounds that show high potency on various field weeds such as Aquinoeno koruga, Callarigusa, Ichibi and Inubu and have selectivity for crops such as corn, wheat, soybeans, and ivy.
  • the compound of the present invention also includes a compound having a growth inhibitory effect on useful plants such as crops, ornamental plants and fruit trees.
  • the compound of the present invention has an excellent herbicidal activity against weeds such as paddy field weeds such as Nobie, Tamagayari, Omodaka and Firefly, and also includes a compound showing selectivity to rice.
  • the compound of the present invention can be applied to the control of weeds in orchards, lawns, track ends, vacant lots and the like.
  • the compounds of the present invention also include those having a plant growth regulating action.
  • the herbicide of the present invention contains one or more of the compounds of the present invention as an active ingredient.
  • the compound of the present invention can be used in a pure form without adding other components, and can be used in the form of a general pesticide for the purpose of using it as a pesticide, that is, a wettable powder, a granule, It can be used in the form of powders, emulsions, aqueous solvents, suspensions, flowables and the like.
  • plant-based powders such as soybean flour and flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc.
  • Organic and inorganic compounds such as fine powder, sodium benzoate, urea and sodium sulfate are used.
  • petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetate , Trichlorethylene, methylisobutyl ketone, mineral oil, vegetable oil, water, etc. are used as solvents.
  • Surfactants can be added, if necessary, to obtain a uniform and stable form in these preparations.
  • the active ingredient concentration in the herbicide of the present invention varies depending on the form of the preparation described above. 5 to 90%, preferably 1) to 85% for wettable powders: 3 to 70%, preferably 5% for emulsions ⁇ 30%: For granules, a concentration of 0.01% to 30%, preferably 0.05% to 10% is used.
  • the wettable powder and emulsion thus obtained are diluted to a predetermined concentration with water to form a suspension or emulsion, and the granules are sprayed on the soil before or after germination of the weeds. Or mixed.
  • an appropriate amount of 0.1 g or more of the active ingredient is applied per 10 ares.
  • the herbicide of the present invention can be used by mixing with known fungicides, insecticides, acaricides, herbicides, plant growth regulators and the like.
  • a higher effect can be expected due to the synergistic action of the mixed drug.
  • a combination with a plurality of known herbicides is also possible.
  • Suitable agents to be used in combination with the herbicide of the present invention include carbamate herbicides such as benthiocarb, molinate and dime pipelet, acid carbomate herbicides, butachlor, pretilachlor, mefenacet and the like.
  • Amide herbicides diphenyl ether herbicides such as chrometoxinil and biphenox, triazine herbicides such as atrazine and cyanadine, sulphonylurea herbicides such as chlorsulfuron and sulfometurone monomethyl, MCP Carboxylic acid-based herbicides such as MCPB, phenoxyphenoxypropionic acid-based herbicides such as diclohop-methyl, pyridyloxy-phenyloxypropionic acid-based herbicides such as fluazifop-butyl, Dinitroaniline, such as trifluralin and pendimethalin Herbicides, urea herbicides such as linuron, diuron, etc .; benzoylaminopropionic acid herbicides such as benzoylprophetyl and flantropethyl; and imidazolinone herbicides such as imazaquin, etc.
  • cyclohexanedioxane such as pyroxifos, Daimron, bentazone, difenzazocoat, nabroanilide, etobenzadide, triazovanamide, kink mouth rack, and ketoxydim, cresodim.
  • Example 5 wettable powder
  • the above components were uniformly mixed and finely pulverized to obtain a wettable powder containing 20% of the active ingredient.
  • the mixture After mixing the above uniformly and finely pulverizing, the mixture is granulated into granules with a diameter of 0.5 to 10 mm. To obtain granules with 5% active ingredient,
  • the herbicidal effect was investigated according to the following criteria and expressed as a weed kill index.
  • the numbers 1, 3, 5, 7, and 9 are intermediate values between 0 and 2, 24, 4, and 6, 6, 88, and 10, respectively.
  • Test example 2 Upland soil treatment
  • a plastic pot having a surface area of 250 cm 2 was filled with field soil, and seeds of Aquino eno coloda, Ichibi and Inubu were sowed and 0.5 cm of cover soil was placed thereon.
  • the following day, the wettable powder diluent shown in Example 5 was evenly sprayed on the soil surface so that the active ingredient amounted to 250 g / ha, and three weeks after the treatment, the herbicidal effect was investigated.
  • Table 10 are shown in Table 10.
  • Test example 3 Paddy foliage treatment
  • the compound of the present invention shows a high herbicidal activity under both the soil treatment and the foliage treatment under upland cropping conditions.
  • it contains compounds that show high potency against various field weeds such as Aquino nokorogosa, Calarigusa, Ichibi and Inubu, and selectivity for crops such as corn, wheat, soybeans and ivy.
  • the compound of the present invention also includes a compound having a growth inhibitory effect on useful plants such as crops, ornamental plants and fruit trees.
  • the compound of the present invention has an excellent herbicidal activity against weeds such as paddy field weeds such as Nobie, Tamagayari, Omodaka and Firefly, and also includes a compound showing selectivity to rice.
  • the compound of the present invention can be applied to the control of weeds in orchards, lawns, track ends, vacant lots and the like.
  • the compounds of the present invention also include those having a plant growth regulating action.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Composés de formule générale (I) dans laquelle A est N ou CR3; Z est O ou S; R1 et R2 sont chacun H, alkyle C1-C6, alcoxy C1-C6, haloalcoxy C1-C6, haloalkyle C1-C6 ou analogue; R3 est H, alkyle C1-C6 ou analogue; R4 et R5 sont chacun H, alkyle C1-C6, cycloalkyle C3-C7, haloalkyle C1-C6 éventuellement substitués ou analogue; R6 est H, alkyle C1-C6, cycloalkyle C3-C7, haloalkyle C1-C6, acyle, tri(alkyle C1-C6) silyle éventuellement substitués ou analogue; et y1 à y8 sont chacun H ou alkyle C1-C6. Lesdits composés présentent une excellente activité herbicide et les compositions les contenant sont utiles en tant qu'herbicides.
PCT/JP1996/001363 1995-05-25 1996-05-23 Derives heterocycliques ayant un groupe hydroxyalkyle phenyle et herbicides Ceased WO1996037491A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU57785/96A AU5778596A (en) 1995-05-25 1996-05-23 Heterocyclic derivatives having hydroxyalkyl phenyl group an d herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP7/150850 1995-05-25
JP7150850A JPH08319286A (ja) 1995-05-25 1995-05-25 ヒドロキシアルキル置換フェニル基を有する複素環誘導体および除草剤

Publications (1)

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WO1996037491A1 true WO1996037491A1 (fr) 1996-11-28

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Application Number Title Priority Date Filing Date
PCT/JP1996/001363 Ceased WO1996037491A1 (fr) 1995-05-25 1996-05-23 Derives heterocycliques ayant un groupe hydroxyalkyle phenyle et herbicides

Country Status (3)

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JP (1) JPH08319286A (fr)
AU (1) AU5778596A (fr)
WO (1) WO1996037491A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04342586A (ja) * 1991-04-17 1992-11-30 Ishihara Sangyo Kaisha Ltd アジン系化合物、それらの製造方法及びそれらを含有する除草剤
WO1994017059A1 (fr) * 1993-01-29 1994-08-04 Nippon Soda Co., Ltd. Derive heterocyclique
WO1996004278A1 (fr) * 1994-08-02 1996-02-15 Nippon Soda Co., Ltd. Derive d'oxazole, son procede de production et herbicide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04342586A (ja) * 1991-04-17 1992-11-30 Ishihara Sangyo Kaisha Ltd アジン系化合物、それらの製造方法及びそれらを含有する除草剤
WO1994017059A1 (fr) * 1993-01-29 1994-08-04 Nippon Soda Co., Ltd. Derive heterocyclique
WO1996004278A1 (fr) * 1994-08-02 1996-02-15 Nippon Soda Co., Ltd. Derive d'oxazole, son procede de production et herbicide

Also Published As

Publication number Publication date
AU5778596A (en) 1996-12-11
JPH08319286A (ja) 1996-12-03

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